The real difference in sea worthiness of motor yachts

Hi Jake. Let's address the elephant in the room: "I’m new to …. boating in general." Once you get near 50' you'll probably be required to hire a captain for the first year and may find you need the captain for several years. I gave a lesson to a fellow and his wife on a 44 and ended up his captain for about 10 years through 4 or 5 boats. He found that he loved driving a boat but hated the stress of docking and realized it paid to have my experience aboard. Also above that size you're probably talking about a 6' draft. Georgia has a lot of shallow water. Since you don't seem to have a planned type of usage in mind yet I'd suggest you look for something under 48' at which size you can probably get by with just lessons, and running aground won't ruin your season.
As for what makes a boat more sea worthy the answer is extremely complex. Size, weight, hull design, hull strength, power, etc, etc.
How do you picture yourself using a boat? Fishing, coastwise cruising, extended cruising, day out on the bay with friends, just hanging out in the marina, party? How many people sleeping aboard? Do you want to run fast (25-30kts $$$$) or relaxed (8-12 kts)?
If this is your first larger boat there's no need to spend anywhere near the budget you have planned, especially if you're planning to get seriously bigger in a few years. Have you thought about your maintenance budget?

It's a lot more complex than that. Let's compare the Prestige 55' and Hatteras 60'. The Hatteras is a lot more comfortable and better built in every aspect. Exterior the teak on the Prestige will need to be replaced in 6-7 years.....the Hatteras teak will go twice as long. Prestige cushions and such will need to be replaced much sooner. Prestige is more maintenance heavy. Hatteras has a flybridge with HVAC that is comfortable all of the time, the Prestige has no HVAC. The interior of the Hatteras is much quieter and you won't hear a lot of noise while you're sleeping. Hatteras holds a lot more fuel and has a lot better range on a tank of fuel. Much better quality build components and easier to source parts for them. Hull design makes more importance to ride than sheer weight.

I can't think of very many planing even as large as 75' MY's that have a 6' draft......besides Riva's........

True, mostly 4.5'-5.5' unless he goes sail, but 6' is close enough as an example. Far too little info to get into specific discussions. Yes Hatteras is better than Prestige, and you could write a book on why, but if he plans to just cruise local waters it's irrelevant. Once had a client who picked up a new 52' Bertram with outriggers and a swim platform to cruise L.I. Sound and occasionally drop a hook for flounder. He liked how it looked. Over $1M and totally the wrong boat.

I ran both a 50' Prestige and a 55' Princess extensively. The 55' Princess Fly is a very capable boat. The lower stations means nothing as regards to having people around you, as they're all behind you while you're in the starboard forward corner running the boat. I'd look at Sunseeker also, as the 52' Manhattan is a very well laid out boat. The Prestige will have you with a lot of frustration with broken parts, waiting on parts, dealing with sub par dealers (as far as even getting parts.) The Princesses have their share of issues as well......The problem is, you don't even begin to know, what you don't know.........

Actually that 26 SR is just what I love to hear. Great training boat. Like a big sail with a single I/O. You know what it's like trying to back that thing up with a cross wind? You probably also know what it feels like to get pounded. that boat probably taught you a lot more than you even realize. For what you're describing 50-60 sounds good, but anything over 40' would do the job. Coming from the SR you'd probably like something that'll cruise at 20-25kts. Look for something with an upper and lower helm like a Princess or Viking sport cruiser or even an express cruiser. There's some nice ones in that range like the Sunseeker Predator. Keep in mind that the bigger you go the harder it is to find slips, especially for lunch stops when playing around the Gulf. Also the closer you are to 50' probably will keep you in around a 3 1/2' draft. which will make life easier in some of the inside waters on the Gulf side and also in the Bahamas. Towards 55' is where you'll start getting to around a 5' draft.

You need to back up a moment from brands to your use, to your desired speed, to your desired range, to your desired draft, to your budget. Then look at boats that fit within those requirements.

The boats you've listed are all semi-displacement so I'm assuming you're looking for that style and speed. If so, I'd put Hatteras among the best. I'd look at Sunseeker and put Princess slightly below. I'd also put Galeon, Prestige, and Beneteau Swift Trawler a step down. As you're looking at used, don't overlook Sea Ray. Might Grand Banks fit your need? Both built a lot of quality boats.

How many people aboard, normally and maximum?

I do not like Hatteras' lack of lower helm but look at the whole picture before dismissing them. Then in the same year, they will cost you more.

You're years if not decades from the Caribbean. You'd be more inclined to do the Great Loop first but definitely US coastal cruising and Bahamas. You'll purchase another boat before you do the Caribbean, if you ever do. Think of that for your second boat but don't let it overly influence this one.

Btw, when and if you head for the Caribbean leave your boat home and charter one, maybe bareboat. You'd be amazed at the sea state you can run into getting down there.

So you've made a lot of trips to the Caribbean and run into those sea states?

I'm surprised you don't know that the Florida Straits are fairly notorious.

I fully know about the Caribbean having spent extensive time in the Eastern and Western. I assume by ignoring my question completely, that you have not and are only stating the notorious part from second and third hand knowledge. I know that traveling to the Eastern Caribbean is made out to be far more treacherous by some who haven't been than it really is. Yes, you need weather windows, but you can island hop your way there.

I also know that the Florida Straits have virtually nothing to do with the Caribbean. The Straits are that narrow area bordered on the East by the Atlantic Ocean, on the West by the Gulf of Mexico, to the North by the Keys and to the South by Cuba. Therefore, they have nothing to do with the Caribbean or the sea states you'd encounter in the Caribbean. Most who travel from Florida to the Caribbean don't go through the straits either although we returned home once from the Eastern Caribbean between the Bahamas and Cuba and you may briefly be in the straits if you're traveling from Key West to the Western Caribbean.

So, any actual experience? What route did you take to the Caribbean when you went?

I ignored you because being a smart ass is beneath you. Some others no but you I expected more of.

You ignored me because you're espousing something on a subject on which you're ignorant. Your way out would have been simply to say you've heard from others but your Florida strait attempt to put me down failed miserably. If you have any actual experience, then share it. Otherwise admit not. I do have experience in the Caribbean. I would warn that the trip from the Turks and Caicos to the Dominican Republic might be very much dependent on waiting for a good weather window. For instance, today, to travel to the Eastern Caribbean would require going through at least 9' seas with short periods, but later in the week and next weekend there are predicted some beautiful sea conditions for a four day period so more than enough time to make the crossing.

Your suggestion of chartering is good for some, but others of us prefer to take our own boats.

You don't want to buy the totally wrong boat. Figure out what you NEED in a boat, think about how you will be using it, where, speed.....are the refrigerators and freezers large enough, is there anywhere outside you can enjoy when it's raining etc. etc.

I have an owner that went down on length on his 19th yacht, ordered it and waited months and month, his wife hates it and two months later he's replacing it.

Your best bet will be chartering a yacht or two or three in this size with a captain for a week each.

A few other brands that might offer suitable boats include Belize, Riviera, Maritomo, Offshore, and Krogen Express.